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161683

Sigma-Aldrich

4-Cyclopentene-1,3-dione

95%

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Synonym(s):
1-Cyclopentene-3,5-dione, 2-Cyclopenten-1,4-dione, 2-Cyclopentene-1,4-dione, Cyclopent-4-en-1,3-dione, Cyclopentene-3,5-dione, Cyclopentenedione
Linear Formula:
C5H4(=O)2
CAS Number:
Molecular Weight:
96.08
Beilstein/REAXYS Number:
2038507
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

solid

bp

60 °C/1 mmHg (lit.)

mp

34-36 °C (lit.)

storage temp.

2-8°C

SMILES string

O=C1CC(=O)C=C1

InChI

1S/C5H4O2/c6-4-1-2-5(7)3-4/h1-2H,3H2

InChI key

MCFZBCCYOPSZLG-UHFFFAOYSA-N

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1 of 4

This Item
797081735329147850
vibrant-m

161683

4-Cyclopentene-1,3-dione

vibrant-m

797081

3-Cyclopenten-1-ol

vibrant-m

735329

(Iodomethyl)cyclopentane

vibrant-m

147850

2-Cyclopenten-1-one ethylene ketal

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

bp

60 °C/1 mmHg (lit.)

bp

-

bp

-

bp

59-62 °C/16 mmHg (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-8°C

mp

34-36 °C (lit.)

mp

-

mp

-

mp

-

form

solid

form

solid

form

liquid

form

liquid

Application

4-Cyclopentene-1,3-dione was used in the synthesis of 2-methoxymethylene-4-cyclopentene-1,3-dione and chrysotrione B (2-acylcyclopentene-1,3-dione derivative). It was used to investigate the influence of sulfiydryl group-specific reagents on activity of bovine heart phospholipid exchange protein.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

183.2 °F - closed cup

flash_point_c

84 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Journal of agricultural and food chemistry, 66(22), 5531-5539 (2018-03-17)
Pathogenic fungi continue to develop resistance against current antifungal drugs. To explore the potential of agricultural waste products as a source of novel antifungal compounds, we obtained an unbiased GC-MS profile of 151 compounds from 16 commercial and experimental cultivars
P E DiCorleto et al.
The Journal of biological chemistry, 254(16), 7795-7802 (1979-08-25)
Two phospholipid exchange proteins from bovine heart have been purified approximately 2000-fold and judged greater than 90% pure. The proteins are similar in molecular weight (both 33,400 by polyacrylamide gel electrophoresis and 23,500 by gel filtration), in amino acid composition
T Bui et al.
Biochimica et biophysica acta, 1397(1), 31-42 (1998-04-18)
The molecular pathways by which the cyclopentenone prostaglandins (PGA and PGJ series) inhibit cell growth and tumorigenicity are poorly understood. These cellular responses may be caused by specific regulation of growth-related and stress-induced genes. A variety of prostaglandins were tested
Yoshihiro Uto et al.
Bioorganic & medicinal chemistry, 16(11), 6042-6053 (2008-05-14)
We designed chiral 2-nitroimidazole derivatives containing a 2-aminomethylene-4-cyclopentene-1,3-dione moiety as antiangiogenic hypoxic cell radiosensitizers. Based on results of molecular orbital calculations, the 2-aminomethylene-4-cyclopentene-1,3-dione moiety is expected to show high electrophilicity comparable to that of the 2-methylene-4-cyclopentene-1,3-dione moiety included in TX-1123
L Lizardi et al.
The Journal of membrane biology, 129(2), 167-178 (1992-08-01)
Voltage-clamp experiments using the three-microelectrode voltage clamp technique were performed on ventroabdominal flexor muscles of the crustacean Atya lanipes. Potassium and chloride currents were found to underlie the normal, passive response of the muscle. Blocking potassium currents with tetraethylammonium and

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